Category: 38380-85-7

Reference of 38380-85-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 38380-85-7 name is 1-Bromo-4-cyclopropoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1: 1-bromo-4-(cyclopropyloxy)benzene (9.5 g, 45 mmol), DMA (66 mL), and MeOH (33 mL) were added to a bomb reactor and degassed by bubbling through argon for 5 minutes. The degassed mixture was charged with DPPF (1.85 g, 3.34 mmol) and Pd(OAc)2 (0.50 g, 2.2 mmol) and degassed under CO. The reaction was heated in the bomb at 15 psi CO at 80C for 18 h. The crude reaction mixture was filtered through celite and concentrated under reducedpressure. The residue was purified by column chromatography on silica gel (5 – 25% EtOAc/hexane) to afford methyl 4-cyclopropoxybenzoate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-cyclopropoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
Ether – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 38380-85-7 as follows. name: 1-Bromo-4-cyclopropoxybenzene

Step 1 : A solution of 1-bromo-4-cyclopropoxybenzene (900 mg, 4.22 mmol) in THF (20 mL, anhydrous) was added n-BuLi (2.5 M, 2.6 mL) at -78C and stirred at -78C for 2 hours under N2. Then, thereto was added dropwise DMF (926 mg, 12.66 mmol, anhydrous) at – 78C and it was stirred for 2 hours. The solution was quenched with NH4Cl (aq. 1 mL) at – 78C and stirred at 0C for 0.5 hour. The mixture was diluted with ethyl acetate (10 mL). The mixture was filtered and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL), washed with brine (3 * 15 mL). The organic layer was dried with anhydrous Na2S04, filtered and concentrated in vacuum to give 4- cyclopropoxybenzaldehyde (700 mg). LC-MS: tR = 0.800 min (method 2), m/z = 162.8 [M + H]+.

According to the analysis of related databases, 38380-85-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 38380-85-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 38380-85-7 name is 1-Bromo-4-cyclopropoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture of 2,4-dibromothiazole (Compound 8A) (3.9 g, 16 mmol), 3,4- dichlorophenylboronic acid (3.05 g, 16 mol), Pd(dppf)C12 (0.7 g, 0.87 mmol), and cesium carbonate (15 g, 46 mmol) in DME (120 mL) and water (10 mL) was heated at reflux under nitrogen overnight. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to yield Compound 8B. LC-MS (ESI) m/z: 308 [M+H]t

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-cyclopropoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 38380-85-7, name is 1-Bromo-4-cyclopropoxybenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 1-Bromo-4-cyclopropoxybenzene

A mixture of intermediate compound 11 (2.34 mmol, 0.5 g), potassium phthalimide (2.81 mmol, 0.52 g) and copper (I) iodide (2.81 mmol, 0.54 g) in dimethylacetamide (6 mL) was refluxed under argon for 18 h. After cooling to room temperature, the reaction mixture was treated with 2N potassium hydroxide (5 mL), and partitioned with EtOAc (25 mL) and saturated 2N potassium hydroxide (25 mL). The organic layer was separated and washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated to afford 547 mg of the title compound which was precipitated in acetonitrile. The solid was filtered and washed with hexane, dried over vacuum to afford 221 mg of the pure title compound (221 mg, Yield: 34%). 1 H NMR (400 MHz, CDCI3) delta 7.98-7.95 (2H, m), 7.80-7.78 (2H, m), 7.36-7.32 (2H, m), 7.20-7.16 (2H, m), 3.80-3.75 (1 H, m), 0.82-0.81 (4H, m) LC-MS: tR= 3.55 [M+H]+ not ion (method 3).

The synthetic route of 1-Bromo-4-cyclopropoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; DRACONIS PHARMA, S.L.; LABORATORIOS DEL DR. ESTEVE, S.A.; AGUILAR, Nuria; FERNANDEZ, Joan, Carles; TERRICABRAS, Emma; CARCELLER GONZALEZ, Elena; GARCIA GARCIA, Francisco, Javier; SALAS SOLANA, Jordi; WO2013/149996; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 38380-85-7, name is 1-Bromo-4-cyclopropoxybenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 1-Bromo-4-cyclopropoxybenzene

Step 1: A solution of 1-bromo-4-cyclopropoxybenzene (900 mg, 4.22 mmol) in THF (20 mL, anhydrous) was added n-BuLi (2.5 M, 2.6 mL) at -78C and stirred at -78C for 2 hours under N2. Then, thereto was added dropwise DMF (926 mg, 12.66 mmol, anhydrous) at – 78C and it was stirred for2 hours. The solution was quenched with NH4CI (aq. lmL) at-78C and stirred at 0C for 0.5 hour. The mixture was diluted with ethyl acetate (10 mL). The mixture was filtered and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL), washed with brine (3 x 15 mL). The organic layer was dried with anhydrous Na2504, filtered and concentrated in vacuum to give 4- cyclopropoxybenzaldehyde (700 mg). LC-MS: tR = 0.800 mm (method 2), m/z = 162.8 [M +H].

The synthetic route of 1-Bromo-4-cyclopropoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

38380-85-7, name is 1-Bromo-4-cyclopropoxybenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 38380-85-7

7?-BuLi (2. 5 M in hexane, 9.76 mL, 24.4 mmol) was added over 17 min to a solution of l-bromo-4-cyclopropoxybenzene (5.0 g, 23.4 mmol) in THF (80 mL) at -78 0C. After 40 min, B(OEt)3 (5.9 mL, 34.3 mmol) was added and the mixture was allowed to reach rt and was stirred at rt for 18 h. The mixture was cooled to 0 0C and HCl (aq, 1 M, 70 mL) was added. After 30 min the mixture was extracted with f-BuOMe (3×50 mL) and the combined extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was washed with petroleum ether to yield the sub-title compound (1.5 g, 34 %).

The synthetic route of 38380-85-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2006/77367; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem